1. Field of the Invention
The present invention relates to a silicon-containing compound; a method for surface treatment of an electrode, using the silicon-containing compound; a surface-treating agent of an electrode, comprising the silicon-containing compound; and an organic electroluminescence device obtained by treating an anode with the silicon-containing compound.
2. Related Art of the Invention
Recently, many studies on electronic or photoelectronic devices using organic materials have intensively been made. However, few devices are composed only of the organic material and, in almost all of cases, a device structure is formed by laminating the organic material and inorganic material. Since such an electronic or photoelectronic device consists of many inorganic/organic interfaces, because it has a structure fabricated by laminating the organic material over the inorganic material in the device, it is important to control of the mechanical and electric characteristics of the interface to improve the device performance.
In an organic electroluminescence device, for example, an inorganic transparent conductive electrode of indium-tin oxide (hereinafter abbreviated to ITO, sometimes), tin oxide (SnO2), zinc oxide (ZnO), etc. is often used as a transparent conductive electrode for transmitting light and injecting holes. The device is constructed by forming a layer of an organic hole transporting material on this transparent conductive electrode, but the interface between the transparent conductive electrode and the organic hole transporting material has the following problem. That is, an ITO electrode, SnO2 electrode or ZnO electrode is used after washing the surface according to solvent washing, plasma washing, etc. and the hydroxyl group or alkoxy group is formed on the surface of the surface-washed ITO electrode, SnO2 electrode or ZnO electrode, thereby hydrophilizing the electrode. Since a hydrophobic functional organic material is generally used as a hole transporting film to be formed on the transparent conductive electrode, peeling of the film arises sometimes because of poor adhesion at the interface. No problem arises when a hydrophilic functional organic molecule is further formed on this hydrophilic conductive electrode. For example, Japanese Patent Kokai Publication No. 2-267888 discloses an organic electroluminescence device obtained by forming a polysilane thin film having the hole transporting property on an ITO electrode. Since a conventional polysilane compound has only a hydrophobic group on the side chain, satisfactory adhesion is still to be obtained, necessarily.
A surface-treating agent represented by a silane coupling agent is widely used as a modifier of the interface between composite materials prepared by using organic materials in combination with inorganic materials, such as elastomer, paint, adhesives, sealant, resin coat, etc., including fiber-reinforced plastic. It becomes possible to improve the adhesion between the inorganic layer and organic layer by treating with this surface-treating agent. Since almost all of surface-treating agent, which have hitherto been used, have no electron transporting property or hole transporting property, it serves only as an electric insulator, thereby to drastically deteriorate performance as the electronic or photoelectronic device.
On the other hand, the work function of the ITO electrode, SnO2 electrode or ZnO electrode hardly agrees with the ionization potential of the organic hole transporting material, and a difference in potential between the transparent conductive electrode and organic hole transporting material arises. This difference in potential becomes an potential barrier to holes in case of injecting holes from the transparent conductive electrode into the organic hole transporting material, sometimes. This potential barrier causes reduction in probability of injection of holes from the transparent conductive electrode to the organic hole transporting material, thereby lowering the injection efficiency of holes. In order to solve this problem, an attempt of vacuum deposition of metal phthalocyanine having an intermediate ionization potential between the work function of the transparent conductive electrode and the ionization potential of the organic hole transporting material in the semitransparent state has been made. However, it is pointed out that the light transmission is lowered because the metal phthalocyanine has absorption in the visible light region.
An object of the present invention is to provide a novel silicon-containing compound; a method for surface treatment of an electrode, using the silicon-containing compound wherein the mechanical/electric contact between an electrode (e.g. transparent conductive electrode, etc.) and an organic layer is improved; an surface-treating agent of an electrode, comprising the silicon-containing compound; and an organic electroluminescence device (hereinafter referred to as an xe2x80x9corganic EL devicexe2x80x9d, sometimes) having excellent mechanical and electric contact between an electrode and an organic layer, which is obtained by treating an anode with the silicon-containing compound.
The present inventors have intensively studied about a surface-treating agent having the hole transporting property so as to solve the above mechanical and electric problems of the conventional technique. As a result, the present inventors have found that the injection efficiency of holes into the organic layer and adhesion can be improved a by treating the surface of the electrode with a specific silicon-containing compound. Thus, the present invention has been accomplished.
The present invention relates to [1] a silicon-containing compound having an oxidation potential of 0.3 to 1.5 V on the basis of a standard hydrogen electrode, wherein at least one alkoxy group is bonded to a silicon atom and at least one aromatic amine group is also bonded to the silicon atom.
Furthermore, the present invention relates to [2] the silicon-containing compound according to the term [1], wherein a structural formula is represented by the general formula (1): 
wherein R1 represents a hydrogen atom, or a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms; R2 represents a straight-chain or branched alkyl group having 1 to 10 carbon atoms; R3 represents a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms; Ar1 represents an arylene group having 6 to 24 carbon atoms; Ar2 represents a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms, or the general formula (2): 
wherein Ar3 represents an arylene group having 6 to 24 carbon atoms; and R4 and R5 independently represent a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms; s and t independently represent an integer from 1 to 3, which satisfy the expression 2xe2x89xa6s+txe2x89xa64; and a ring may be independently formed between R3 and Ar1, R3 and Ar2, or Ar1 and Ar2, or alternatively a ring may be independently formed between R4 and Ar3, or R4 and R5 when Ar2 is represented by the general formula (2).
Also, the present invention relates to [3] a method for surface treatment of an electrode in a device having an organic layer in contact with the electrode, which comprises treating the surface of the electrode with the silicon-containing compound of the term [1] or [2] or a silicon-containing compound which has an oxidation potential of 0.3 to 1.5 V on the basis of a standard hydrogen electrode and is represented by the following general formula (3): 
wherein R1, R2, s and t are the same as those defined in the general formula (1); and A represents a condensed polycyclic aromatic group having 14 to 30 carbon atoms.
Also, the present invention relates to [4] a surface-treating agent of an electrode, comprising the silicon-containing compound of the above term [1] or [2] or the silicon-containing compound represented by the general formula (3) of the term [3].
Also, the present invention relates to [5] an organic electroluminescence device comprising a pair of electrodes of an anode and a cathode, at least one of which is transparent or semitransparent, and at least one organic layer formed between the electrodes, wherein the anode is treated with the silicon-containing compound of the term [1] or [2] or the silicon-containing compound represented by the general formula (3) of the term [3].
The silicon-containing compound of the present invention is characterized by a silicon-containing compound having an oxidation potential (hereinafter referred to as xe2x80x9cEoxxe2x80x9d, sometimes) of 0.3 to 1.5 V on the basis of a standard hydrogen electrode, wherein at least one alkoxy group is bonded to a silicon atom and at least one aromatic amine group is also bonded to the silicon atom. The oxidation potential is preferably from 0.5 to 1.1 V.
Furthermore, the silicon-containing compound used as the surface-treating agent of the electrode of the present invention is characterized by the above silicon-containing compound with an aromatic amine group on the silicon atom, or a silicon-containing compound represented by the following general formula (3), wherein an oxidation potential on the basis of a standard hydrogen electrode is from 0.3 to 1.5 V. The oxidation potential is preferably from 0.5 to 1.1. As the silicon-containing compound used as the surface-treating agent of the electrode of the present invention, the above silicon-containing compound with an aromatic amine group on the silicon atom is preferable.
In the present invention, the silicon-containing compound having the oxidation potential is within this range is preferable, because holes to be injected from the electrode into the organic layer easily be injected into the organic layer via the silicon-containing compound and, therefore, the injection efficiency of holes is improved.
For example, Eox can be determined from a half-wave potential of a first oxidation wave of voltamogram obtained with an electrochemical measurement, e.g. cyclic voltammetry, etc. Specifically, cyclic voltammetry is performed by dissolving a surface-treating agent in an organic solvent containing a suitable supporting electrolyte, e.g. 0.1 N solution of tetrabutylammonium tetrafluoroborate in dichloromethane, using a pair of platinum electrodes as a working electrode and a counter electrode, and using a silver/silver chloride electrode, a saturated calomel electrode, a standard hydrogen electrode, etc. as a reference electrode. A concentration of the silicon-containing compound of the present invention may be selected so that the oxidation wave curve can be easily detected.
A lower-value voltage at the point of intersections of a straight line, which is drawn parallel to a base line at the half-height between a peak of the first oxidation wave curve and base line on the resulting cyclic voltamogram, and an oxidation wave may be taken as Eox.
In the silicon-containing compound whose structural formula is represented by the above general formula (1), the group of R1 other than the hydrogen atom is a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms, preferably a straight-chain or branched alkyl group having 1 to 10 carbon atoms.
The aryl and aralkyl groups may be substituted with a straight-chain or branched alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 6. carbon atoms or less. Specific examples of the substituent of the aryl and aralkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, cyclohexyl group, etc., preferably methyl group and ethyl group.
Specific examples of R1 other than the hydrogen atom include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, etc.; cycloalkyl groups such as cyclohexyl group, etc.; aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, etc.; and aralkyl groups such as benzyl group, phenethyl group, p-methylbenzyl group, etc.; preferably methyl group, ethyl group, n-propyl group, isopropyl group and n-butyl group.
In the silicon-containing compound represented by the general formula (1), R2 is a straight-chain or branched alkyl group having 1 to 10 carbon atoms, preferably a straight-chain or branched alkyl group having 1 to 3 carbon atoms.
Specific examples of R2 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, etc., preferably methyl group and ethyl group.
In the silicon-containing compound represented by the general formula (1), R3 is a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms, preferably a phenyl group.
Specific examples of R3 include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, etc.; cycloalkyl groups such as cyclohexyl group, etc.; aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, etc.; and aralkyl groups such as benzyl group, phenethyl group, p-methylbenzyl group, etc.
In the silicon-containing compound represented by the general formula (1), Ar1 is an arylene group having 6 to 24 carbon atoms. Specific examples thereof include phenylene, naphthylene and biphenylene groups, preferably a phenylene group.
In the silicon-containing compound represented by the general formula (1), Ar2 is a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less or an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms. Specific examples thereof include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexylgroup, octyl group, dodecyl group, etc.; cycloalkyl groups such as cyclohexyl group, etc.; aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, etc.; and aralkyl groups such as benzyl group, phenethyl group, p-methylbenzyl group, etc. Among them, a phenyl group is particularly preferable.
In the silicon-containing compound represented by the general formula (1), when Ar2 is represented by the general formula (2), R4 and R5 independently represent a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms, preferably an aryl group having 6 to 24 carbon atoms, particularly a phenyl group.
Specifically, R4 and R5 independently represent alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, etc.; cycloalkyl groups such as cyclohexyl group, etc.; aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, etc.; and aralkyl groups such as benzyl group, phenethyl group, p-methylbenzyl group, etc.
In the silicon-containing compound represented by the general formula (1), when Ar2 is represented by the general formula (2), an arylene group Ar3 is an arylene group having 6 to 24 carbon atoms. Specific examples thereof include phenylene, naphthylene and biphenylene groups, more preferably phenylene and biphenylene groups, particularly a biphenylene group.
In R3, R4, R5 and Ar2, the alkyl and cycloalkyl groups may be substituted with a straight-chain or branched alkoxy group having 1 to 6 carbon atoms, amino group, nitro group, cyano group, ester group, halogen and the like. Specific examples of the substituent of the alkyl and cycloalkyl groups include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, cyclohexyl group, etc., preferably methoxy group and ethoxy group.
In R3, R4, R5, Ar2, Ar2 and Ar3, the aryl group(e.g.the phenyl group),the aralkyl group and the arylene group (e.g.the phenylene group,the biphenylene group) may be substituted with a straight-chain or branched alkyl or alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 6 carbon atoms or less, amino group, nitro group, cyano group, ester group, halogen and the like. Specific examples of the substituent of the aryl, aralkyl and arylene groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, cyclohexyl group, etc., preferably methyl group, ethyl group, methoxy group and ethoxy group.
In the above silicon-containing compound represented by the general formula (3), A is preferably a condensed polycyclic aromatic group comprising of 3 to 8 benzene rings, more preferably a condensed polycyclic aromatic group comprising of 4 to 6 benzene rings. Specific examples of A include a pyrenyl group, a triphenylenyl group, naphthacenyl group, a perylenyl group and the like. The condensed polycyclic aromatic group having 14 to 30 carbon atoms may be substituted with a straight-chain or branched alkyl or alkoxy group having 1 to 6 carbon atoms, a cycloalkyl group having 6 carbon atoms or less, amino group, nitro group, cyano group, ester group, halogen and the like. Specific examples of the substituent of the condensed polycyclic aromatic group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, cyclohexyl group, etc., preferably methyl group, ethyl group, methoxy group and ethoxy group.
Specific examples of the silicon-containing compound of the present invention and silicon-containing compound used as a surface-treating agent of the electrode of the present invention are described below, but are not limited thereto. In the following formulas, R6and R7independently represent methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group or dodecyl group; and R8 to R16 independently represent methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, cyclohexyl group, amino group, nitro group, cyano group, methyl ester group or fluorine atom. The symbol m is 0 or 1; n is an integer of 0 to 2; o is an integer of 0 to 3; p is an integer of 0 to 4; and q is an integer of 0 to 5. When hydrogen atoms of one group are substituted with two or more substituents, those substituents may be the same or different. 
In the silicon-containing compounds represented by the general formulas (1) and (3) of the present invention, s and t may independently represent an integer from 1 to 3, which satisfy the expression 2xe2x89xa6s+txe2x89xa64.
Specific examples of the silicon-containing compounds represented by the general formulas (1) and (3) in the present invention are described below, but are not limited to these compounds. N-phenyl-N-(4-triethoxy silyl phenyl)-amino benzene, N-(4-diethoxymethyl silyl phenyl)-N-phenylamino benzene, N-(4-dimethylethoxy silyl phenyl)-N-phenylamino benzene, N-phenyl-N-(4-trimethoxy silyl phenyl)-amino benzene, N-(4-dimethoxymethyl silyl phenyl)-N-phenylamino benzene, N-(4-dimethylmethoxy silyl phenyl)-N-phenylamino benzene, N-(4xe2x80x2-methylphenyl)-N-(4-triethoxy silyl phenyl)-amino benzene, N-(4-diethoxymethyl silyl phenyl)-N-(4xe2x80x2-methylphenyl)-amino benzene, N-(4-dimethylethoxy silyl phenyl )-N-(4xe2x80x2-methylphenyl)-amino benzene, N-(4xe2x80x2-methylphenyl)-N-(4-trimethoxy silyl phenyl)-amino benzene, N-(4-dimethoxymethyl silyl phenyl)-N-(4xe2x80x2-methylphenyl)-amino benzene, N-(4-dimethylmethoxy silyl phenyl)-N-(4xe2x80x2-methylphenyl)-amino benzene, N-(4xe2x80x3-methylphenyl)-N-(4-triethoxy silyl phenyl)-4-methyl amino benzene, N-(4xe2x80x2-diethoxymethyl silyl phenyl)-N-(4xe2x80x3-methylphenyl)-4-methyl amino benzene, N-(4xe2x80x2-dimethylethoxy silyl phenyl)-N-(4xe2x80x3-methylphenyl)-4-methyl amino benzene, N-(4xe2x80x3-methylphenyl)-N-(4xe2x80x2-trimethoxy silyl phenyl)-4-methyl amino benzene, N-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N-(4xe2x80x3-methylphenyl)-4-methyl amino benzene, N-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N-(4xe2x80x2-methylphenyl)-4-methyl amino benzene, Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x2-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,4-benzene diamine, N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,4-benzene. diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,4-benzene diamine, N,Nxe2x80x2-di(4xe2x80x3-methylphenyl)-N-phenyl-Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,Nxe2x80x2-di(4xe2x80x3-methylphenyl)-N-phenyl-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,Nxe2x80x2-di(4xe2x80x3-methylphenyl)-N-phenyl-1,4-benzene diamine, N,Nxe2x80x2-di(4xe2x80x3-methylphenyl)-N-phenyl-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,4-benzene diamine, N,Nxe2x80x2-di(4xe2x80x3-methylphenyl)-Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N-phenyl-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,Nxe2x80x2-di(4xe2x80x3-methylphenyl)-N-phenyl-1,4-benzene diamine, N,N-di(4xe2x80x3-methylphenyl)-Nxe2x80x2-phenyl-Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N-di(4xe2x80x3-methylphenyl)-Nxe2x80x2-phenyl-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N-di(4xe2x80x3-methylphenyl)-Nxe2x80x2-phenyl-1,4-benzene diamine, N,N-di(4xe2x80x3-methylphenyl)-Nxe2x80x2-phenyl-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,4-benzene diamine, N,N-di(4xe2x80x3-methylphenyl)-Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-Nxe2x80x2-phenyl-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N-di(4xe2x80x3-methylphenyl)-Nxe2x80x2-phenyl-1,4-benzene diamine, N,N-diphenyl-Nxe2x80x2-(4xe2x80x3-methylphenyl)-Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N-diphenyl-Nxe2x80x2-(4xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N-diphenyl-Nxe2x80x2-(4xe2x80x3-methylphenyl)-1,4-benzene diamine, N,N-diphenyl-Nxe2x80x2-(4xe2x80x3-methylphenyl)-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N-diphenyl-Nxe2x80x2-(4xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N-diphenyl-Nxe2x80x2-(4xe2x80x3-methylphenyl)-1,4-benzene diamine, N,Nxe2x80x2-diphenyl-N-(4xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,Nxe2x80x2-diphenyl-N-(4xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,Nxe2x80x2-diphenyl-N-(4xe2x80x3-methylphenyl)-1,4-benzene diamine, N,Nxe2x80x2-diphenyl-N-(4xe2x80x3-methylphenyl)-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,Nxe2x80x2-diphenyl-N-(4xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,Nxe2x80x2-diphenyl-N-(4xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3,4xe2x80x3,6xe2x80x3-trimethylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3,4xe2x80x3,6xe2x80x3-trimethylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3,4xe2x80x3,6xe2x80x3-trimethylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4-trimethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3,4xe2x80x3,6xe2x80x3-trimethylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3,4xe2x80x3,6xe2x80x3-trimethylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3,4xe2x80x3,6xe2x80x3-trimethylphenyl)-1,4-benzene diamine, N,N,Nxe2x80x2-tri(4xe2x80x3-ethylphenyl)-Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-ethylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-ethylphenyl)-1,4-benzene diamine, N,N,Nxe2x80x2-tri(4xe2x80x3-ethylphenyl)-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-ethylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-ethylphenyl)-1,4-benzene diamine, N,N,Nxe2x80x2-tri(3xe2x80x3,5xe2x80x3-dimethylphenyl)-Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3,5xe2x80x3-dimethylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3,5xe2x80x3-dimethylphenyl)-1,4-benzene diamine, N,N,Nxe2x80x2-tri(3xe2x80x3,5xe2x80x3-dimethylphenyl)-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3,5xe2x80x3-dimethylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3,5xe2x80x3-dimethylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3-methylphenyl)-1,4-benzene diamine, N,N,Nxe2x80x2-tri(3xe2x80x3-methylphenyl)-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methoxyphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methoxyphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methoxyphenyl)-1,4-benzene diamine, N,N,Nxe2x80x2-tri(4xe2x80x3-methoxyphenyl)-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methoxyphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methoxyphenyl)-1,4-benzene diamine, 3-methyl-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, 3-methyl-Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, 3-methyl-Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, 3-methyl-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, 3-methyl-Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diamine, 3-methyl-Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,4-benzene diaminei 3-methyl-Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,4-benzene diamine, 3-methyl-Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,4-benzene diamine, 3-methyl-Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,4-benzene diamine, 3-methyl-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,4-benzene diamine, 3-methyl-Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,4-benzene diamine, 3-methyl-Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,4-benzene diamine, Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,3-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,3-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,3-benzene diamine, Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,3-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,3-benzene diamine, N-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,3-benzene diamine, Nxe2x80x2-(4xe2x80x2-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,3-benzene diamine, Nxe2x80x2-(4xe2x80x2-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,3-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,3-benzene diamine, N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,3-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,3-benzene diamine, Nxe2x80x2-(4xe2x80x2-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3-methylphenyl)-1,3-benzene diamine, Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x2xe2x80x3-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x2-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,Nxe2x80x2-di(4xe2x80x3xe2x80x2-methylphenyl)-N-phenyl-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,Nxe2x80x2-di(4xe2x80x3xe2x80x2-methylphenyl)-N-phenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,Nxe2x80x2-di(4xe2x80x3xe2x80x2-methylphenyl)-N-phenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,Nxe2x80x2-di(4xe2x80x3xe2x80x2-methylphenyl)-N-phenyl-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,Nxe2x80x2-di(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N-phenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,Nxe2x80x2-di(4xe2x80x3xe2x80x2-methylphenyl)-N-phenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N-di(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-phenyl-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N-di(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-phenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N-di(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-phenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N-di(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-phenyl-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N-di(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-Nxe2x80x2-phenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N-di(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-phenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N-diphenyl-Nxe2x80x2-(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N-diphenyl-N,-(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N-diphenyl-Nxe2x80x2-(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N-diphenyl-Nxe2x80x2-(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N-diphenyl-Nxe2x80x2-(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N-diphenyl-Nxe2x80x2-(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,Nxe2x80x2-diphenyl-N-(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,Nxe2x80x2-diphenyl-N-(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,Nxe2x80x2-diphenyl-N-(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,Nxe2x80x2-diphenyl-N-(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,Nxe2x80x2-diphenyl-N-(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x95x90-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,Nxe2x80x2-diphenyl-N-(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3xe2x80x2,4xe2x80x3xe2x80x2,6xe2x80x3xe2x80x2-trimethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3xe2x80x2,4xe2x80x3xe2x80x2,6xe2x80x3xe2x80x2-trimethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x2-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3xe2x80x2,4xe2x80x3xe2x80x2,6xe2x80x3xe2x80x2-trimethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3xe2x80x2,4xe2x80x3xe2x80x2,6xe2x80x3xe2x80x2-trimethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(2xe2x80x3xe2x80x2,4xe2x80x3xe2x80x2,6xe2x80x3xe2x80x2-trimethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2tri(2xe2x80x3xe2x80x2,4xe2x80x3xe2x80x2,6xe2x80x3xe2x80x2-trimethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-ethylphenyl)-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-ethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-ethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-ethylphenyl)-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-ethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-ethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2,5xe2x80x3xe2x80x2-dimethylphenyl)-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2,5xe2x80x3xe2x80x2-dimethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2,5xe2x80x3xe2x80x2-dimethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2,5xe2x80x3xe2x80x2-dimethylphenyl)-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2,5xe2x80x3xe2x80x2-dimethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2,5xe2x80x3xe2x80x2-dimethylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(3xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methoxyphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methoxyphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methoxyphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methoxyphenyl)-Nxe2x80x2-(4,4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methoxyphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methoxyphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 3,3xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, 2,2xe2x80x2-dimethyl-Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-trenphenyl-1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl-silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl 1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-triphenyl 1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-triphenyl-1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-triethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-diethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-Nxe2x80x2-(4xe2x80x3-trimethoxy silyl phenyl)-1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethoxymethyl silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, Nxe2x80x2-(4xe2x80x3-dimethylmethoxy silyl phenyl)-N,N,Nxe2x80x2-tri(4xe2x80x3xe2x80x2-methylphenyl)-1,1xe2x80x2-biphenyl-3,3xe2x80x2-diamine, 1-(triethoxysilyl)-pyrene, 1-(diethoxymethyl silyl)-pyrene, 1-(dimethylethoxy silyl)-pyrene, 1-(trimethoxy silyl)-pyrene, 1-(dimethoxymethyl silyl)-pyrene, 1-(dimethylmethoxy silyl)-pyrene, 2-(triethoxysilyl)-pyrene, 2-(diethoxymethyl silyl)-pyrene, 2-(dimethylethoxy silyl)-pyrene, 2-(trimethoxy silyl)-pyrene, 2-(dimethoxymethyl silyl)-pyrene, 2-(dimethylmethoxy silyl)-pyrene, 4-(triethoxysilyl)-pyrene, 4-(diethoxymethyl silyl)-pyrene, 4-(dimethylethoxy silyl)-pyrene, 4-(trimethoxy silyl)-pyrene, 4-(dimethoxymethyl silyl)-pyrene, 4-(dimethylmethoxy silyl)-pyrene, 1-(triethoxysilyl)-naphthacene, 1-(diethoxymethyl silyl)-naphthacene, 1-(dimethylethoxy silyl)-naphthacene, 1-(trimethoxy silyl)-naphthacene, 1-(dimethoxymethyl silyl)-naphthacene, 1-(dimethylmethoxy silyl)-naphthacene, 2-(triethoxysilyl)-naphthacene, 2-(diethoxymethyl silyl)-naphthacene, 2-(dimethylethoxy silyl)-naphthacene, 2-(trimethoxy silyl)-naphthacene, 2-(dimethoxymethyl silyl)-naphthacene, 2-(dimethylmethoxy silyl)-naphthacene, 5-(triethoxysilyl)-naphthacene, 5-(diethoxymethyl silyl)-naphthacene, 5-(dimethylethoxy silyl)-naphthacene, 5-(trimethoxy silyl)-naphthacene, 5-(dimethoxymethyl silyl)-naphthacene, 5-(dimethylmethoxy silyl)-naphthacene, 1-(triethoxysilyl)-triphenylene 1-(diethoxymethyl silyl)-triphenylene, 1-(dimethylethoxy silyl)-triphenylene, 1-(trimethoxy silyl)-triphenylene, 1-(dimethoxymethyl silyl)-triphenylene, 1-(dimethylmethoxy silyl)-triphenylene, 2-(triethoxysilyl)-triphenylene, 2-(diethoxymethyl silyl)-triphenylene, 2-(dimethylethoxy silyl)-triphenylene, 2-(trimethoxy silyl)-triphenylene, 2-(dimethoxymethyl silyl)-triphenylene, 2-(dimethylmethoxy silyl)-triphenylene, 1-(triethoxysilyl)-perylene, 1-(diethoxymethyl silyl)-perylene, 1-(dimethylethoxy silyl)-perylene, 1-(trimethoxy silyl)-perylene, 1-(dimethoxymethyl silyl)-perylene, 1-(dimethylmethoxy silyl)-perylene, 2-(triethoxysilyl)-perylene, 2-(diethoxymethyl silyl)-perylene, 2-(dimethylethoxy silyl)-perylene, 2-(trimethoxy silyl)-perylene, 2-(dimethoxymethyl silyl)-perylene, 2-(dimethylmethoxy silyl)-perylene, 3-(triethoxysilyl)-perylene, 3-(diethoxymethyl silyl)-perylene, 3-(dimethylethoxy silyl)-perylene, 3-(trimethoxy silyl)-perylene, 3-(dimethoxymethyl silyl)-perylene, 3-(dimethylmethoxy silyl)-perylene.
The silicon-containing compound of the present invention and silicon-containing compound used as a surface-treating agent of the electrode of the present invention can be synthesized by various methods. For example, when the silicon-containing compound has an aromatic amine group on the silicon atom, the compound can be synthesized by the method shown in the following reaction scheme. 
wherein R1 to R3, Ar1, Ar2, t and s are as defined above; R17 represents an alkyl group; X represents a halogen atom; and Y represents a halogen atom or an alkoxy group.
That is, as shown in the reaction scheme, a halogenated amine compound represented by the formula [b] can be obtained by reacting an amine compound represented by the formula [a], produced by a known method, at a temperature within the range preferably from xe2x88x9220 to 150xc2x0 C.,more preferably from 0 to 100xc2x0 C., most preferably from 10 to 60xc2x0 C., for preferably 30 minutes to 24 hours, more preferably from 2 to 18 hours, most preferably from 4 to 10 hours to directly halogenate Ar1, using a halogenating agent such as N-bromosuccinimide, bromine, pyridinium hydrobromide perbromide, etc. The halogen atom is not specifically limited, and may be fluorine atom, chlorine atom, bromine atom or iodine atom. Examples of a solvent for synthesis of the halogenated amine compound represented by the formula [b] include carbon tetrachloride, N,N-dimethylformamide, acetic acid and the like.
Then, carbon atoms to which the halogen atom is linked are subjected to lithiation or Grignard reaction by reacting the halogenated amine compound [b] with an organolithium reagent [c] or metal magnesium [d] to obtain a lithium compound represented by the formula [e] or a Grignard compound represented by the formula [f].
As the method, a known method can be used. For example, in case of the lithiation, the above halogenated amine compound [b] is dissolved in an ether solvent and then an equimolar amount of an organolithium reagent is added dropwise to the solution. A dropping temperature is from preferably xe2x88x9280 to 0xc2x0 C., more preferably from xe2x88x9280 to xe2x88x9220xc2x0 C., most preferably from xe2x88x9280 to xe2x88x9240xc2x0 C. A reaction time is preferably from 10 minutes to 10 hours, more preferably from 30 minutes to 6 hours, most preferably from 1 to 3 hours.
Examples of the ether solvent to be used include diethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, dioxane, diisopropyl ether, di-n-butyl ether and the like.
Examples of the organolithium reagent to be used include n-butyllithium, sec-butyllithium, tert-butyllithium, methyllithium, lithium diisopropylamide and the like. These organolithium reagents are used after diluting with an organic solvent.
Also in case of the Grignard reaction, the same solvent as that used in case of the lithiation can be used. Firstly, an equimolar to two-fold molar amount of a metal magnesium and a solvent are charged in a reaction vessel and a solution prepared by diluting the above halogenated amine compound [b] with a solvent is added dropwise. Then, the Grignard reaction is performed by stirring at a temperature within the range preferably from 0 to 150xc2x0 C., more preferably from 25 to 100xc2x0 C., most preferably from 50 to 80xc2x0 C. for preferably 1 to 24 hours, more preferably from 3 to 18 hours, most preferably from 5 to 10 hours.
Furthermore, the compound represented by the general formula (1) of the present invention can be obtained by reacting the above lithium compound [e] or a Grignard compound [f] with an alkoxysilane compound represented by the formula [g] by using a known method. A reaction temperature is preferably from xe2x88x9280 to 0xc2x0 C.,more preferably from xe2x88x9280 to xe2x88x9220xc2x0 C., most preferably from xe2x88x9280 to xe2x88x9240xc2x0 C. A reaction time is preferably from 10 minutes to 10 hours, more preferably from 30 minutes to 6 hours, most preferably from 1 to 3 hours.
The silicon-containing compound having a condensed polycyclic aromatic group on the silicon atom, which is used as a surface-treating agent of the electrode of the present invention, can also be produced by the method shown in the following reaction scheme. 
wherein R1, R2, A, t and s are as defined above; R17 represents an alkyl group; X represents a halogen atom; and Y represents a halogen atom or an alkoxy group.
That is, as shown in the reaction scheme, a halogenated condensed polycyclic aromatic compound represented by the formula (bxe2x80x2) can be obtained by reacting a condensed polycyclic aromatic compound represented by the formula (axe2x80x2), produced by a known method, at a temperature within the range preferably from xe2x88x9220 to 150xc2x0 C., more preferably from 0 to 100xc2x0 C.,most preferably from 10 to 60xc2x0 C., for preferably 30 minutes to 24 hours, more preferably from 2 to 18 hours, most preferably from 4 to 10 hours to directly halogenate a condensed polycyclic aromatic group A, using a halogenating agent such as N-bromosuccinimide, bromine, pyridinium hydrobromide perbromide, etc. The halogen atom is not specifically limited, and may be fluorine atom, chlorine atom, bromine atom or iodine atom. Examples of a solvent for synthesis of the halogenated condensed polycyclic aromatic compound represented by the formula (bxe2x80x2) include carbon tetrachloride, N,N-dimethylformamide, acetic acid and the like.
Then, carbon atoms to which the halogen atom is linked are subjected to lithiation or Grignard reaction by reacting the halogenated condensed polycyclic aromatic compound (bxe2x80x2) with an organolithium reagent (cxe2x80x2) or metal magnesium (dxe2x80x2) to obtain a lithium compound represented by the formula (exe2x80x2) or a Grignard compound represented by the formula (fxe2x80x2).
As the method, a known method can be used. For example, in case of the lithiation, the above halogenated condensed polycyclic aromatic compound (b"") is dissolved in an ether solvent and then an equimolar amount of an organolithium reagent is added dropwise to the solution. A dropping temperature is preferably from xe2x88x9280 to 0xc2x0 C., more preferably from xe2x88x9280 to xe2x88x9220xc2x0 C., most preferably from xe2x88x9280 to xe2x88x9240xc2x0 C. A reaction time is from preferably 10 minutes to 10 hours, preferably from more 30 minutes to 6 hours, most preferably from 1 to 3 hours.
Examples of the ether solvent to be used include diethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, dioxane, diisopropyl ether, di-n-butyl ether and the like.
Examples of the organolithium reagent to be used include n-butyllithium, sec-butyllithium, tert-butyllithium, methyllithium, lithium diisopropylamide and the like. These organolithium reagents are used after diluting with an organic solvent.
Also in case of the Grignard reaction, the same solvent as that used in case of the lithiation can be used. Firstly, an equimolar to two-fold molar amount of metal magnesium and a solvent are charged in a reaction vessel and a solution prepared by diluting the above halogenated condensed polycyclic aromatic compound (bxe2x80x2) with a solvent is added dropwise. Then, the Grignard reaction is performed by stirring at a temperature within the range preferably from 0 to 150xc2x0 C., more preferably from 25 to 100xc2x0 C., most preferably from 50 to 80xc2x0 C. for preferably 1 to 24 hours, more preferably from 3 to 18 hours, most preferably from 5 to 10 hours.
Furthermore, the compound represented by the general formula (3) of the present invention can be obtained by reacting the above lithium compound (exe2x80x2) or a Grignard compound (fxe2x80x2) with an alkoxysilane compound represented by the formula (gxe2x80x2) by using a known method. A reaction temperature is preferably from xe2x88x9280 to 0xc2x0 C., more preferably from xe2x88x9280 to xe2x88x9220xc2x0 C., most preferably from xe2x88x9280 to xe2x88x9240xc2x0 C. A reaction time is from preferably 10 minutes to 10 hours, more preferably from 30 minutes to 6 hours, most preferably from 1 to 3 hours.
A solvent used in the reaction of the alkoxysilane compound may be any one capable of dissolving a raw material and a reaction product, and is not specifically limited. For example, there can be used aromatic hydrocarbons such as toluene, xylene, benzene, etc.; aliphatic hydrocarbons such as dodecane, heptane, hexane, cyclohexane, etc.; and ether solvents such as diethyl ether, tetrahydrofuran, tetrahydropyran, diethylene glycol dimethyl ether, dioxane, etc.
In the present invention, since the alkoxysilane compound used in the production of the silicon-containing compound is apt to be easily hydrolyzed in case of using in the reaction, the reaction may be preferably performed under an inert atmosphere containing no water, such as dry nitrogen, argon, etc. so that no water is introduced. Furthermore, water in the solvent for the above reaction is preferably removed. When the water content is large, alkoxy groups of the raw material and product are hydrolyzed and polycondensated, which results in decrease of the yield of the desired product.
The reaction product obtained by the above reaction is preferably used after purifying by a known method such as recrystallization, distillation, column chromatography and the like.
In the present invention, a method of treating the surface of an electrode (e.g. transparent conductive electrode, etc.) with a silicon-containing compound can be performed by diluting the silicon-containing compound with a suitable solvent to prepare a treating-solution and bringing the treating-solution into contact with the electrode.
The solvent used for dilution may be any one capable of dissolving the silicon-containing compound, and is not specifically limited. For example, there can be used aromatic hydrocarbons such as toluene, xylene, benzene, etc.; aliphatic hydrocarbons such as dodecane, heptane, hexane, cyclohexane, etc.; and ether solvents such as diethyl ether, tetrahydrofuran, tetrahydropyran, diethylene glycol dimethyl ether, dioxane, etc.
In the present invention, the concentration of the silicon-containing compound in the treating-solution is not specifically limited as far as the silicon-containing compound is dissolved, but is preferably from 0.1 to 20% by weight, more preferably from 0.5 to 10% by weight. It is also possible to add a catalyst to this treating-solution, if necessary. Examples of the catalyst include ammonia, trimethylamine, triethylamine and a N-alkyl-substituted compound of piperazine or piperidine. An amount of the catalyst added is preferably from 0.1 to 10% by weight.
A method of treating the electrode by contacting with the treating-solution is not specifically limited, but a method of immersing the electrode in the treating-solution in an inert atmosphere containing no water (e.g. dry nitrogen, argon, etc.) is preferable.
Furthermore, the electrode after treatment is preferably used after the compound remaining reacted with the electrode is removed by washing with a solvent capable of dissolving the silicon-containing compound and/or a solvent which is inert to the silicon-containing compound (e.g. acetone, etc.).
In the present invention, as the electrode to be treated with the silicon-containing compound, various materials having conductivity can be used. Examples of the material include {circumflex over (1)} metal, {circumflex over (2)} glass or plastic on which a metal thin film is formed, {circumflex over (3)} conductive polymer and the like. Specific examples of the metal include aluminum, copper, tin, platinum, gold, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, indium, stainless steel, brass and the like. Examples of the metal thin film to be formed on the surface of glass or plastic include thin films of the above metals. Examples of the conductive polymer include polyaniline, polyacetylene and the like.
In the present invention, when a transparent or semitransparent electrode is used as the electrode to be treated with the silicon-containing compound, conductive metal oxide films and semitransparent thin films of the above mentioned metals are used. Specifically, films composed of indium oxide-tin (ITO), tin oxide, zinc oxide, etc. and semitransparent thin films of aluminum, copper, tin, platinum, gold, silver, vanadium, molybdenum, chromium, cadmium, titanium, nickel, indium, stainless steel, brass, etc. are used. In the present invention, an electrode on which an oxide is formed is preferable. Specific examples thereof include film made by using the above metal oxide and thin metal films wherein an oxide film is naturally formed on the metal surface, etc.
Examples of the method of producing a thin film include vacuum deposition method, sputtering method, plating method and the like.
In the present invention, the surface of the electrode to be treated with the silicon-containing compound is preferably cleaned by using treating methods such as acid or alkaline washing, detergent washing, solvent washing, plasma washing, ozone treatment, ultraviolet irradiation, ultraviolet irradiation under an ozone atmosphere, etc. alone or in combination thereof before performing the surface treatment.
The organic EL device of the present invention will be described hereinafter.
The structure of the organic EL device of the present invention may be any organic EL device having at least one organic layer between a pair of electrodes of an anode and a cathode, at least one of which is transparent or semitransparent, wherein the anode is treated with the surface-treating agent of the present invention, and is not specifically limited. Therefore, any known structure can be employed. Alternatively, various modifications can be made without departing from the scope of the present invention.
Specific examples of the structure of the organic EL device of the present invention include {circle around (1)} device structure having a pair of electrodes on both sides of a light emitting layer, {circle around (2)} device structure made by laminating a light emitting layer and a hole transporting layer and providing an cathode on the surface of the light emitting layer and an anode on the surface of the hole transporting layer, {circle around (3)} device structure made by laminating a light emitting layer and an electron transporting layer and providing an anode on the surface of the light emitting layer and a cathode on the surface of the electron transporting layer, {circle around (4)} device structure made by laminating a hole transporting layer, a light emitting layer and an electron transporting layer in this order and providing an anode on the surface of the hole transporting layer and a cathode on the surface of the electron transporting layer.
In all of device structures, the light emitting layer contains a light emitting material, or a light emitting material and a charge transporting material (hole transporting material and/or electron transporting material), the hole transporting layer contains a hole transporting material, and the electron transporting layer contains an electron transporting material.
The shape, size, material and fabrication method of the organic EL devices having these structures of the present invention are appropriately selected according to applications of the organic EL device, and are not specifically limited.
With respect to the light emitting layer, hole transporting layer and electron transporting layer, the case where a single layer is used and the case where a plurality of layers are used in combination are also included in the present invention.
The hole transporting material used in the organic EL device of the present invention is not specifically limited, and known materials can be used. Examples of the hole transporting material include low molecular weight compounds such as pyrazoline derivative, arylamine derivative, stilbene derivative, etc.; and polymeric compounds such as poly (N-vinylcarbazole), polysilane, etc. Specifically, N,Nxe2x80x2-di(3xe2x80x3-methylphenyl)-N,Nxe2x80x2-diphenyl-1,1xe2x80x2-biphenyl-4,4xe2x80x2-diamine is preferable as the low molecular weight compound, and poly (N-vinylcarbazole) and polysilane compound are preferable as the polymeric compound.
When the hole transporting material and the light emitting material are used in a mixture, an amount of the hole transporting material and light emitting material used varies depending on the kind of the compound to be used. Therefore, the amount is appropriately decided as far as sufficient film forming property and light emitting characteristics are not inhibited. The amount of the hole transporting material is normally from 1 to 40% by weight, preferably from 2 to 30% by weight, based on the light emitting material.
The polysilane compound, which can be used as the hole transporting layer or the hole transporting material of a layer containing the hole transporting material and light emitting material, may contain one or more repeating units represented by the following general formula (4): 
wherein R18 and R19 independently represent an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms, and/or a repeating unit represented by the following general formula (5): 
wherein R20 represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms; R21 represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms; Ar4 represents an arylene group having 6 to 24 carbon atoms; Ar5 represents an aryl group having 6 to 24 carbon atoms; and a ring may be formed between Ar4 and Ar5, Ar4 and R21, or R21 and Ar5.
R18, R19, R20 or R21 in the repeating units represented by the general formulas (4) and (5) independently represent a straight-chain or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 10 carbon atoms or less, an aryl group having 6 to 24 carbon atoms or an aralkyl group having 7 to 26 carbon atoms. R21 is preferably an aryl group having 6 to 24 carbon atoms, particularly a phenyl group.
In R18,R19,R20 and R21, the aryl(e.g.the phenyl group)-and aralkyl groups may be substituted with a straight-chain or branched alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 6 carbon atoms or less. Specific examples of the substituent of the aryl and aralkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, cyclohexyl group, etc., preferably methyl group and ethyl group.
Specific examples of R18, R19, R20 or R21 independently include alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, etc.; cycloalkyl groups such as cyclohexyl group, etc.; aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, etc.; and aralkyl groups such as benzyl group, phenethyl group, p-methylbenzyl group, etc.
Ar4 in the repeating unit represented by the general formula (5) is preferably an arylene group having 6 to 24 carbon atoms. Specific examples thereof a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, etc., preferably a phenylene group.
Ar5 in the repeating unit represented by the general formula (5) is preferably an aryl group having 6 to 24 carbon atoms. Specific examples thereof a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, etc., preferably a phenyl group.
The arylene group for Ar4 and the aryl group for Ar5 may be substituted with a straight-chain or branched alkyl group having 1 to 6 carbon atoms and a cycloalkyl group having 6 carbon atoms or less. Specific examples of the substituent of the arylene and aryl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, cyclohexyl group, etc., preferably methyl group and ethyl group.
In the present invention, Ip1 preferably satisfies the following numeral formula (I):
Wxe2x89xa6Ip1xe2x89xa6Ip2xe2x80x83xe2x80x83(I)
wherein Ip1 is an ionization potential of a silicon-containing compound; W is a work function of an anode to be treated with the silicon-containing compound; and Ip2 is an ionization potential of an organic layer to be formed on the anode to be treated with the silicon-containing compound.
Ip1 more preferably satisfies the following numeral formula (II):
Ip1≈(W+Ip2)/2xe2x80x83xe2x80x83(II)
In the present invention, holes to be injected from an anode such as transparent conductive electrode into an organic layer adjacent to the anode pass through a two-stage process of injection to a hole transporting arylamine derivative structure and/or a condensed polycyclic aromatic ring contained in the silicon-containing compound of the present invention and further injection to the organic layer. In each injection process, holes must be injected over an potential barrier of Ip1-W and Ip2-Ip1. If Ip1 satisfies the above formula, each potential barrier of the hole injection process becomes smaller than an potential barrier Ip2-W between the anode and the organic layer. Therefore, holes easily are injected and the injection efficiency of holes to be injected from the anode to the organic layer is improved.
In the present invention, when the ionization potential Ip1 of the silicon-containing compound satisfies the expression W greater than Ip1 or Ip1 greater than Ip2, the potential of any hole injection process is larger than the potential barrier Ip2-W between the anode and the organic layer and holes do not be injected easily. Therefore, the injection efficiency of holes to be injected from the anode to the organic layer is sometimes lowered.
A method of producing a polysilane compound used as the hole transporting material of the organic electroluminescence device of the present invention is not specifically limited, but the same method as that described in Journal of Organometallic Chemistry, Vol. C27, page 198 (1980) or Journal of Polymer Science: Polymer Chemistry Edition, Vol. 22, page 159 (1984) can be used.
That is, a polysilane compound containing at least one repeating unit represented by the above general formula (4) and/or a repeating unit represented by the above general formula (5) on the main skeleton can be produced by bringing a dihalosilane monomer represented by the following general formula (6): 
wherein R18 and R19 are as defined above; and X represents a halogen atom, or a dihalosilane monomer represented by the following general formula (7): 
wherein R20, R21, Ar4 and Ar5 are as defined above; and X represents a halogen atom, or a mixture of two or more kinds of dihalosilane monomers having different side chain, represented by the above general formula (6) and/or a dihalosilane monomer represented by the above general formula (7), into contact with a condensed catalyst of an alkaline metal to perform dehalogenation and polycondensation under a high-purity inert atmosphere wherein oxygen and water are removed.
The light emitting material of the light emitting layer used in the organic EL device of the present invention, or the light emitting material of the layer containing the hole transporting material and light emitting material is not specifically limited, and various materials can be applied. A light emitting low molecular weight compound and a light emitting polymer are preferable, and the light emitting polymer is more preferable.
The light emitting low molecular weight compound is not specifically limited, and there can be used naphthalene and a derivative thereof; anthracene and a derivative thereof; perylene and a derivative thereof; a polymethine, coumarine and cyanine pigments; 8-hydroxyquinoline and a metal complex of a derivative thereof; a aromatic amine; and tetraphenylcyclopentane and a derivative thereof. Specifically, there can be known light emitting low molecular weight compounds described in Japanese Patent Kokai Publication Nos. 57-51781 and 59-194393.
The light emitting polymer, which can be used as the light emitting material, is not specifically limited, and examples thereof include polyphenylenevinylene, polyarylene, polyalkylthiophene, polyalkylfluorene and the like. Particularly, the following polyphenylenevinylene derivative is preferable.
The light emitting polymer used preferably in the light emitting layer of theorganic EL device of the present invention will be explained hereinafter.
The light emitting polymer is a polymer containing a repeating unit represented by the following general formula (8): in an amount of 50% by mol based on the whole repeating unit 
wherein Ar6 represents an arylene group or a heterocyclic compound group having 4 to 20 carbon atoms which take part in a conjugated bond; R22 and R23 independently represent a group selected from the group consisting of hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heterocyclic compound group having 4 to 20 carbon atoms and cyano group. The repeating unit represented by the general formula (8) is preferably not less than 70% based on the whole repeating unit, although it depends on the structure of the repeating unit. The light emitting polymer may contain a divalent aromatic compound group or a derivative thereof, a divalent heterocyclic compound group or a derivative thereof, and a group obtained by combining them, as a repeating unit other than the repeating unit represented by the general formula (8). Furthermore, the repeating unit represented by the general formula (8) and other repeating unit may be linked in a non-conjugated unit having an ether group, an ester group, an amide group, an imide group, etc., or the non-conjugated portion may be contained in the repeating unit.
In the light emitting polymer used in the organic EL device of the present invention, Ar6 of the general formula (8) is an arylene group or a heterocyclic compound group having 4 to 20 carbon atoms which take part in a conjugated bond, and examples thereof include a divalent aromatic compound group or a group of a derivative thereof, divalent heterocyclic compound group or a group of a derivative thereof, which are described below, and a group obtained by combining them. 
wherein R24 to R115 independently represent a group selected from the group consisting of hydrogen, alkyl, alkoxy and alkylthio groups having 1 to 20 carbon atoms, aryl and aryloxy groups having 6 to 18 carbon atom and heterocyclic compound group having 4 to 14 carbon atoms.
Among them, phenylene group, substitited-phenylene group, biphenylene group, substituted-biphenylene group, naphthalenediyl group, substituted-naphthalenediyl group, anthracene-9,10-diyl group, substituted-anthracene-9,10-diyl group, pyridine-2,5-diyl group, thienylene group or substituted-thienylene group is preferable. More preferable groups are phenylene group, biphenylene group, naphthalenediyl group, pyridine-2,5-diyl and thienylene group.
When R22 and R23 of the general formula (8) is a substituent other than the hydrogen or cyano group, examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, lauryl group, etc., preferably methyl group, ethyl group, pentyl group, hexyl group, heptyl group and octyl group. Examples of the aryl group include phenyl group, 4-C1-C12 alkoxyphenyl group (C1-C12 shows 1 to 12 carbon atoms, the same rule applies correspondingly to the following), 4-C1-C12alkylphenyl group, 1-naphthyl group, 2-naphthyl group and the like.
In view of the solubility in organic solvents, Ar6of the general formula (8) has preferably one or more groups selected from the group consisting of alkyl, alkoxy or alkylthio group having 4 to 20 carbon atoms, aryl or aryloxy group having 6 to 18 carbon atoms, and heterocyclic compound group having 4 to 14 carbon atoms.
Examples of these groups are as follows. Examples of the alkyl group having 4 to 20 carbon atoms include n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, decyl group, lauryl group, etc., preferably pentyl group, hexyl group, heptyl group and octyl group.
Examples of the alkoxy group having 4 to 20 carbon atoms include butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group, lauryloxy group, etc., preferably pentyloxy group, hexyoxyl group, heptyloxy group and octyloxy group.
Examples of the alkylthio group include butylthio group, pentylthio group, hexylthio group, heptylthio group, octylthio group, decylthio group, laurylthio group, preferably pentylthio group, hexylthio group, heptylthio group, octylthio group and the like.
Examples of the aryl group include phenyl group, 4-C1-C12 alkoxyphenyl group (C1-C12 shows that the number of carbon atoms is any one of 1 to 12), 4-C1-C12alkylphenyl group, 1-naphthyl group, 2-naphthyl group and the like.
Examples of the aryloxy group include phenoxy group. Examples of the heterocyclic compound group include 2-thienyl group, 2-pyrrolyl group, 2-furyl group, 2-, 3- or 4-pyridyl group and the like.
The number of these substituents varies depending on the molecular weight of the light emitting polymer and construction of the repeating unit. In order to obtain a light emitting polymer having high solubility, the number of these substituents is preferably at least one per molecular weight of 600.
The light emitting polymer used in the organic EL device of the present invention may be a random, block or graft copolymer, or a polymer having an intermediate construction of them, e.g. a random copolymer having a block polymer tendency. In order to obtain a light emitting polymer having high quantum yield of fluorescence, the random copolymer having a block polymer tendency, or block or graft copolymer is preferable than a completely random copolymer.
Since the organic EL device of the present invention utilizes light emission from a thin film, a light emitting polymer having luminescence at the solid state is used.
Examples of the good solvent to the light emitting polymer include chloroform, methylene chloride, dichloroethane, tetrahydrofuran, toluene, xylene and the like. The light emitting polymer can be normally dissolved in these solvents in an amount of not less than 0.1% by weight, although it varies depending on the structure or molecular weight of the light emitting polymer.
The polystyrene-reduced molecular weight of the light emitting polymer used in the organic EL device of the present invention is preferably within the range from 103 to 107, and the degree of polymerization depends on the repeated structure and it""s proportion. In view of the film forming property, the total number of the repeated structures is preferably within the range from 4 to 10000, more preferably from 5 to 3000, particularly from 10 to 200.
In the organic EL device of the present invention, when an electron transporting layer is further formed between the light emitting layer and cathode, an electron transporting material used in the electron transporting layer or used, together with the hole transporting material and light emitting material, has a function of transporting electron injected from the cathode to the light emitting layer. The electron transporting material is not specifically limited, and any electron transporting material can be used by selected from compounds which have hitherto been known.
Preferred examples of the electron transporting material include nitro-substituted fluorenone derivative, anthraquinodimethane derivative, diphenylquinone derivative, thiopyran dioxide derivative, heterocyclic tetracarboxylic anhydride, carbodiimide and the like.
Furthermore, preferred examples are fluorenylidene derivative, anthraquinodimethane derivative, anthrone derivative, oxadiazole derivative and the like. Although a metal complex of 8-hydroxyquinoline and a derivative thereof are disclosed as the material for forming the light emitting layer, they can also be used as the electron transporting material.
Next, a typical method of producing the organic EL device having a laminated structure. as one embodiment of the present invention will be described. As the pair of transparent or semitransparent electrodes composed of the anode and cathode, for example, those obtained by forming a transparent or semitransparent electrode on a transparent substrate such as transparent glass, transparent plastic, etc. can be used.
As the material of the anode, for example, there can be used conductive metal oxide films, semitransparent metal thin films and the like. Specifically, films made by indium-tin oxide (ITO), tin oxide, zinc oxide, Au, Pt, Ag, Cu, etc. are used. Examples of the production method include vacuum deposition method, sputtering method, plating method and the like.
These anodes are used after surface-treating with the above silicon-containing compound by using the above treating method.
In the present invention, a hole transporting layer containing a hole transporting material is formed on the anode treated with the silicon-containing compound. Examples of the method of forming the hole transporting layer include method of depositing the hole transporting material as a layer according to the vacuum deposition method, and method of forming a film by application of a coating solution prepared by dissolving the hole transporting material in a solvent or a coating solution prepared by dissolving a binder resin and the hole transporting material in a solvent. When the hole transporting material is a polymeric compound (e.g. polysilane compound, etc.), the method of forming a film by application is preferable.
The coating solution for forming the hole transporting layer by application can be prepared by dissolving the hole transporting material in the solvent, or dissolving the hole transporting material and binder resin in the solvent. The hole transporting layer can be formed by applying the coating solution, using a known method such as dipping method, spray coating method, wire bar coating method, doctor blade coating method, roll coating method, spin coating method and the like. It is preferable to dry with heating at a temperature within the range preferably from 30 to 300xc2x0 C., more preferably from 60 to 200xc2x0 C., under reduced pressure or an inert atmosphere after forming the hole transporting layer.
As the binder resin in which the hole transporting material is dispersed, various resins can be used and examples thereof include polycarbonate resin, polyarylate resin, polysulfone resin, polystyrene, polyacrylate resin, styrene-acrylic copolymer, ethylene-vinyl acetate copolymer, polypropylene resin, olefin polymer, polyvinyl chloride resin, vinyl chloride-vinyl acetate copolymer, polyester resin, alkyd resin, polyamide resin, polyurethane resin, epoxy resin, diallyl phthalate resin, silicone resin, ketone resin, polyvinyl butyral resin, polyether resin, phenol resin, phtotosetting resins (e.g. epoxyacrylate resin ,etc.) and the like. These binder resins can be used alone or in combination thereof.
The solvent, which is used for preparing the coating solution for forming the hole transporting layer, may be any one which dissolves the hole transporting material and binder resin, and various organic solvents can be used. Examples thereof include solvents such as alcohols (e.g. methanol, ethanol, isopropanol, etc.), aliphatic hydrocarbons (e.g. n-hexane, octane, cyclohexane, etc.), aromatic hydrocarbons (e.g. benzene, toluene, xylene, etc.), halogenated hydrocarbons (e.g. dichloromethane, dichloroethane, carbon tetrachloride, chlorobenzene, etc.), ethers (e.g. dimethyl ether, diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, etc.), ketones (e.g. acetone, methyl ethyl ketone, cyclohexanone, etc.), N,Nxe2x80x2-dimethylformamide, dimethyl sulfoxide, etc. These solvents may be used alone or in combination thereof.
As the hole transporting layer, two or more known hole transporting materials may be used in combination. Alternatively, a second hole transporting layer may be formed adjacent to the hole transporting layer formed on the anode.
A film thickness of the hole transporting layer is preferably within the range from 1 nm to 1 xcexcm, more preferably from 2 to 500 nm. In order to enhance the electroluminescence efficiency(luminance/current density) by increasing the current density, the film thickness is most preferably within the range from 5 to 100 nm.
Then, a light emitting layer containing an organic pigment having low molecular weight, a light emitting polymer, etc. as the light emitting material is formed. Examples of the method of forming the light emitting layer include a method of applying a melt, a solution or a mixed solution of these materials according to a spin coating method, a casting method, a dipping method, a bar coating method, roll coating method and the like. It is preferable to form a film by applying the solution or mixed solution according to a coating method such as spin coating method, casting method, dipping method, bar coating method, roll coating method and the like.
A film thickness of the light emitting layer is preferably within the range from 1 nm to 1 xcexcm, more preferably from 2 to 500 nm. In order to enhance the electroluminescence efficiency by increasing the current density, the film thickness is preferably within the range from 5 to 100 nm.
When a thin film of the light emitting layer is formed by the application method, it is preferable to dry with heating at a temperature within the range preferably from 30 to 300xc2x0 C., more preferably from 60 to 200xc2x0 C., under reduced pressure or an inert atmosphere so as to remove the solvent after formation of the hole transporting layer and/or light emitting layer.
When an electron transporting layer is further laminated on the light emitting layer, it is preferable to form the electron transporting layer after the light emitting layer was formed by the above-described film forming method.
The method of forming the film of the electron transporting layer is not specifically limited, and there can be used vacuum deposition method in the powder state; application method such as spin coating method, casting method, dipping method, bar coating method, roll coating method, etc. after dissolving in the solution; or application method such as spin coating method, casting method, dipping method, bar coating method, roll coating method, etc. after mixing the polymeric compound with the electron transporting material in the solution or molten state, followed by dispersion.
The polymeric compound to be mixed is not specifically limited, but those which do not inhibit electron transport are preferable. Those whose absorption to visible light is not strong are preferably used.
Examples thereof include poly(N-vinylcarbazole) and a derivative thereof, polyaniline and a derivative thereof, polythiophene and a derivative thereof, poly(p-phenylenevinylene) and a derivative thereof, poly(2,5-thienylenevinylene) and a derivative thereof, polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like. It is preferable to use the application method when using the polymeric compound because a film can be easily formed.
A film thickness of the electron transporting layer must be a thickness so that no pin hole is formed. When the film thickness is too large, the resistance of the device increase to require high driving voltage, unfavorably. Accordingly, the film thickness of the electron transporting layer is preferably within the range from 1 nm to 1 xcexcm, more preferably from 2 to 500 nm, most preferably from 5 to 100 nm.
Then, an electrode is formed on the light emitting layer or electron transporting layer. This electrode serves as an electron injection cathode. The material is not specifically limited, but a material having small work function is preferable.
For example, there can be used Al, In, Mg, Ca, Li, Mgxe2x80x94Ag alloy, Inxe2x80x94Ag alloy, Mgxe2x80x94In alloy, Mgxe2x80x94Al alloy, Mgxe2x80x94Li alloy, Alxe2x80x94Li alloy, graphite thin film and the like. As the method of producing the cathode, there can be used vacuum deposition method, sputtering method and the like.
In the organic EL device of the present invention, there is also used a method of forming an organic layer containing the hole transporting material and light. emitting or an organic material containing the hole transporting material, light emitting layer and electron transporting material on one electrode according to the same manner as that of forming the above hole transporting layer, and then forming the other electrode.
Since the organic EL device of the present invention is capable of forming the hole transporting layer and light emitting layer by the application method, an organic EL device having low driving voltage, high luminance and high electroluminescence efficiency can be easily fabricated through a simple production process.
The silicon-containing compound of the present invention is industrially useful as a surface-treating agent for improving mechanical and electric contact between an electrode and an organic layer of devices having an organic layer adjacent to the electrode (e.g. transparent conductive electrode, etc.) such as photoconductive device, organic electroluminescence device, spatial light modulator device, organic photoelectric conversion device and the like.